A country town on a hill, it is located between the valleys of the Arbia, Elsa and Pesa Rivers. The territory of its commune is entirely within the Chianti Classico district. Its town centre is among the most important of the Chianti district and it is a holiday resort undergoing constant development. Of Etruscan and Roman origins, a fiefof the nobles of Trebbio (I I th century), it then became an important Florentine military garrison.
The seat of local government for the ancientLeague of Chianti with Radda and Gaiole in the 13th century,later, during the 14th and15th centuries,Castellina was the scene of raids and pillaging. The Florentines built the town walls between 1400 and 1402. Dominated by the historic Fortress, witha very tall defensive building (and overlooked by an even more majestic keep) it presents fortifications and medieval passages,such as the charming Via delleVolte.

The inhabited area conservers, in part, its 14th century character, and the countryside has many farmhouses from the era of the Grand Dukes and also before their reign. Not far from the centre of Castellina there

is a large Etruscan tomb which dates back to the 6thcentury before Christ. It is the most interestinglocal archaeological discovery, a witness to the very ancient presenceof humanity in Chianti. The churches in the surrounding area are numerous and allinteresting. Of particular interest are the church of San Martino a Cispiano, with has conserved all of its Romanesque grace, with a beautiful apse and single nave, and that of San Leonino in Conio,which holds a "Madonna andChild" by Lorenzo di Bicci. The village of Fonterutoli, cited in a document from 998, has a long and interesting history.
The peace agreement between Siena and Florence was signed in 1201 in its church of San Miniato, which has now been destroyed